This grant application describes a research program directed at the development of new synthetic technologies for organic synthesis and molecular diversity construction. Specifically, the proposed research aims to explore the synthetic potential of the DMP and IBX reagents and to develop synthetic technologies based on the photo-induced chemistry of o- substituted benzaldehydes and the reactivity of alpha-sulfonated carbonyl compounds, both in solution and on solid phase. Applications of the developed technologies to total synthesis and combinatorial chemistry are also proposed. The designed and synthesized compounds will be screened against a variety of biological assays for lead identification as a means to facilitate chemical biology studies and drug discovery programs in oncology and other disease areas.